Pyridine → HCID 11736048, compound

HRID 1957944Notes

Reaction equation

HRID 1957944 reaction equation
[C:1]([NH:6][CH:7]([CH3:11])[C:8]([OH:10])=O)(=[O:5])[CH2:2][CH2:3][CH3:4].[O:12]1[CH2:16][CH2:15]C[CH2:13]1.N1C=CC=CC=1.C([O-])(O)=[O:24].[Na+]>CN(C1C=CN=CC=1)C.CO>[C:1]([NH:6][CH:7]([CH3:11])[C:8](=[O:10])[C:13]([O:12][CH2:16][CH3:15])=[O:24])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 11194480N-Butyrylalanine

Product 1

HCID 11736048HCID 11736048, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

The compound of formula VI (3.18 g, 0.02 mol) was dissolved into dried tetrahydrofuran (20 mL), followed by addition of DMAP (0.08 g, 0.6 mmol) and pyridine (5 mL) therein. The mixture was heated for 30 minutes at 50° C., and then cooled. Under ice bath, ethyl oxalyl monochloride (5.46 g, 0.04 mol) was slowly dropped therein. After the dropping, the mixture was heated for 4 hours at 70° C. The solid was filtered off and the solvent was evaporated off under reduced pressure. Water (40 mL) was added therein, and the product was extracted by using ethyl acetate (75 mL×3). The liquid was separated, and the combined organic phase was washed by water (30 mL) and saturated saline (30 mL×2) respectively, and dried over anhydrous sodium sulfate. After the solvent therein was removed by rotary evaporation, NaHCO3 (1.26 g, 0.015 mol) and methanol (20 mL) were added therein, and the mixture was refluxed for 2 hours. After filtration, the solvent was removed by evaporation under reduced pressure to give a yellow oil, i.e., ethyl 3-butyramido-2-oxo-butyrate, which is directly used in the next step without purification.

Workup

  1. temperaturecooled
  2. temperatureAfter the dropping, the mixture was heated for 4 hours at 70° C
  3. filtrationThe solid was filtered off
  4. customthe solvent was evaporated off under reduced pressure
  5. additionWater (40 mL) was added
  6. extractionthe product was extracted
  7. customThe liquid was separated
  8. washthe combined organic phase was washed by water (30 mL) and saturated saline (30 mL×2) respectively
  9. dry with materialdried over anhydrous sodium sulfate
  10. additionwere added
  11. temperaturethe mixture was refluxed for 2 hours
  12. filtrationAfter filtration
  13. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-12c71f8475ad41d19faae5b2a8337442
Source dataset
uspto-grants-2013_04
Patent number
US08410098B2

Reaction notes

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